This copy is for your personal non-commercial use only. To order presentation-ready copies of Toronto Star content for distribution to colleagues, clients or customers, or inquire about permissions/licensing, please go to: www.TorontoStarReprints.com

If Holly Golightly and Captain Jack Sparrow were ever to have crossed storylines, their love child might be Samantha Michelle.

A bit of a pirate, with a taste for classic movies and Johnnie Walker Black who has spent the past few years roaming the high seas in search of bounty and adventure, the young heiress to the Windsor Arms Hotel has a personal style that manages to be both swashbuckling and reminiscent of Audrey Hepburn in Breakfast at Tiffany’s.

How fortunate for us then that Michelle has just returned from London with a ship’s load of booty and installed it in a small, leopard print-swathed corner of the Windsor Arms lobby just in time for dress-up season.

Fittingly, Michelle’s new vintage boutique, which displays almost as much attitude as its young proprietress, is called The Treasure Chest.

“The whole concept of the boutique is that it has absolutely nothing that you need, but everything that you can’t live without,” says Michelle, who personally searched out each glittering beaded bag and fabulous animal print fur on the racks from her favourite vintage haunts in London and dragged them across the Atlantic in her very own, presumably colossally overweight, suitcases.

Article Continued Below

Reflecting the go-big-or-go-home personal style of its mistress, the boutique’s offerings are decidedly eccentric: a shimmering collection of big-shouldered, beaded ’80s tops worthy of the cast of Dynasty (“ ’80s takes on the ’20s,” she notes), next to fun faux furs and dashing swing coats. “This one’s straight out of Rent,” says Michelle, pulling on a ladylike mohair with fur trim that looks très Boheme over black tights and well-worn biker’s boots.

“Pants are complicated, so I just decided I wouldn’t even go there,” says Michelle, who often throws her own bold looks together with a fabulous top, coat or jacket, and whatever she might happen to find comfortable that day underneath. (The day of our shoot, it’s a pair of silk bloomers and black tights.)

“Jackets and coats are really everything,” says Michelle. “In my London apartment, I had three rails along each wall and they were all crammed with coats.

“Anyway, for things like pants and T-shirts, I always just go to the Gap. I love the Gap.”

Taking a page from Michelle and saving on separates while splurging on outerwear and statement pieces is a style formula that is both penny-wise and high-impact, particularly for dressing up during the ever-challenging party season.

At this year’s TIFF InStyle party, held annually at her family’s hotel, Michelle (who, like Eloise in the Kay Thompson children’s books, actually lives in the Windsor Arms) came down to join the party in a pair of men’s pjs and lady’s opera gloves under one of her fave vintage leopard coats.

“Leopard is so naughty,” she says. “The best thing is to wear it in a completely unexpected way.”

When it comes to matters of style, “juxtaposition is the most important thing in life.”

Next to leopard — and leopard on leopard — which features prominently in both the decor scheme as well as the offerings at The Treasure Chest (particularly in the massive boudoir-like change room), Michelle loves black with blue, long gloves, and red nails and lips (of late, Stila’s “Fiery”).

“I see it as war paint,” she says. “It’s important to be battle-ready and feel confident and pretty for whatever’s going down that day.”

What Michelle has zero time for is design-name snobbery — “I’m not into labels” — and the insecurity of those inclined to follow prescribed fashion trends. “Deal with your fear elsewhere,” she says. “Don’t bring it into my sacred space.”

Rather Michelle hopes to encourage the fun and art of pulling it together, with vintage styles worn in new and unusual ways. “The idea is that this is a place to play dress-up and make-believe.”

Part of what makes vintage clothing the ideal plaything, as far as Michelle is concerned, is that it already comes with its own secret story. “Everything here was already owned by somebody else and it’s still a mystery.”

Being among old things is “like walking down an ancient street in an old city — the whole of history is so much bigger than you. It makes you feel like you exist within this greater trajectory of being a creative person in the world.”

At least for now, the adventuring Michelle plans to keep her ship close to shore. “If you can allow yourself to go off into a world of your imagination, things already look different,” she says. “You don’t have to go anywhere, just allow your inner self to indulge.”

And this month, even the most brazen style pirates can feel good about it: 10 per cent of all sales at The Treasure Chest will benefit the Peter Munk Cardiac Centre.

More from the Toronto Star & Partners

LOADING

Copyright owned or licensed by Toronto Star Newspapers Limited. All rights reserved. Republication or distribution of this content is expressly prohibited without the prior written consent of Toronto Star Newspapers Limited and/or its licensors. To order copies of Toronto Star articles, please go to: www.TorontoStarReprints.com